OAN Staff Blake Wolf
11:36 AM – Wednesday, May 14, 2025
Sean “Diddy” Combs’ former girlfriend, Cassy Ventura, gave a heartfelt testimonial against the now-disgraced rapper, further revealing the ways that Combs assaulted and humiliated her throughout their entire relationship.
Ventura met Combs in 2005 when she was just 19-years-old and he was 37.
At the time, Ventura was a young aspiring singer and model attempting to break into the entertainment industry. Her relationship with Combs provided a significant boost for her music career, although it came with dark consequences behind closed doors.
Combs played a significant role in the release of Ventura’s debut single “Me & U.” Although the song was written and produced by Ryan Leslie, it was released through a partnership between Leslie’s NextSelection Lifestyle Group and Diddy’s “Bad Boy Records.”
Diddy promoted the song and helped propel it to commercial success. “Me & U” peaked at number three on the Billboard Hot 100 and was certified platinum — marking a major milestone in Cassie’s early music career.
Meanwhile, Ventura, now 38-years-old, gave her recent testimony in court on the graphic and violent drug-fueled “freak off” sex sessions that Combs insisted she take part in at his request.
“Within the first year of our relationship, Sean proposed to me this idea, this sexual encounter he called voyeurism, where he would watch me… [engage in] sexual activity with another person, specifically another man,” she stated.
Ventura stated that she felt compelled to comply with Combs’ demands, as failure to do so would have resulted in significant hardship for her.
“I was confused, nervous, but I also loved him very much, and I wanted to make him happy,” she continued.
Ventura revealed that in one instance, an alcohol fueled freak-off resulted in Combs physically assaulting her, which resulted in a black eye. She also further claimed that in another instance, she attempted to escape from him, running to an elevator, before ultimately ending up on the ground while he kicked her—referencing the now infamous video of her and Diddy in a hotel.
Later in the testimony, prosecutors played the disturbing video footage from 2016, showing Combs assaulting her in a Los Angeles hotel hallway.
When given the opportunity to speak again, she recounted that Diddy provided her with a “blue dolphin” ecstasy pill during their first intimate encounter, after which such “freak offs” became a frequent occurrence.
“Pretty quickly over time, I knew it wasn’t something I wanted to be doing, especially as regularly as it became,” Ventura stated. “Eventually, it became a job for me pretty much.”
“The freak-offs became a job where there was no space to do anything else but to recover and try to feel normal again,” she stated. “Staying up for days on end, taking drugs, other substances. Drinking. Having sex with a stranger.”
“Thirty-six, 48, 78 hours. The longest ever was four days, maybe even more, on and off with the breaks. It was significant,” she added. “I was recovering from the drugs, dehydration, just staying awake all that time.”
Ventura also revealed that she would frequently get urinary tract infections (UTI) from the freak offs, stating: “I had a lot of stomach issues, gastrointestinal issues from taking drugs.. I’d get frequent UTIs, if you’ve had one you know how painful that is.”
“When we were having frequent freak offs sometimes they were back to back, I couldn’t get rid of it and I was doing the freak off with an infection,” she added. “Occasionally I’d get sores on my tongue from freak offs from the substances and just friction in my mouth.”
Ventura also testified that Combs “humiliated her” by urinating on her. However, this assertion appears to slightly conflict with the testimony of a male escort given at the trial’s start, in which he claimed that Cassie herself had explicitly requested that he urinate on her.
“Sometimes Sean, he himself or the escort, would urinate on me,” she stated in a solemn tone. “Sean urinated at the same time.”
She also disturbingly noted that when the male escorts would pee in her mouth, “it was overwhelming.”
“I choked,” she continued.
Combs and Ventura avoided eye contact throughout the day. When she entered the courtroom, he glanced at her at one point — but she kept her gaze fixed straight ahead. Now 38-years-old, Ventura is pregnant with her third child and is married to Alex Fine, Combs’ former personal trainer.
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